Kissimmee Lakefront Park Grassy waterfront park with walking paths, a fishing pier, picnic pavilions, and a shaded playground. children's playgrounds, splash pad

Search Cottages in Winter Garden

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Winter Garden cottages

House (2 Bedrooms) | Interior

Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is €471
includes taxes & fees
12 Jul - 13 Jul
Fire Pit & Yard: Updated Winter Garden Home!
The Garden, Pet Friendly | Terrace/patio

Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (37 reviews)
"Very clean room, quaint, close to the downtown area. "
United States
Raymond
The price is €157
includes taxes & fees
23 Jun - 24 Jun
Historic Tremain Cottages
Interior

Downtown Cottage

Downtown Cottage
Colonialtown North
8.2 out of 10, Very good, (11 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is €169
includes taxes & fees
14 Jun - 15 Jun
Downtown Cottage
Exterior

Poolside Weekday Retreat – Just 119 Night!

Poolside Weekday Retreat – Just 119 Night!
Lake Mary
9.8 out of 10, Exceptional, (54 reviews)
"Everything was wonderful! We loved the location and the house was cozy and comfortable. "
United States
Mike B.
The price is €248
includes taxes & fees
30 Jun - 1 Jul
Poolside Weekday Retreat – Just 119 Night!
House (4 Bedrooms) | Interior

Pool Access! Spacious Home Near Wekiwa Springs

Pool Access! Spacious Home Near Wekiwa Springs
3.0 star property
Apopka
The price is €352
includes taxes & fees
19 Jun - 20 Jun
Pool Access! Spacious Home Near Wekiwa Springs
Exterior

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
9.8 out of 10, Exceptional, (38 reviews)
"Beautiful property in a fantastic location! We've booking this stay twice and will be back again."
United States
Lisa
The price is €296
includes taxes & fees
14 Jun - 15 Jun
Incredible Private Lakefront Cottage Retreat
Terrace/patio

Charming Cottage Retreat – Just 100 a Night Midweek Special Early Check In

Charming Cottage Retreat – Just 100 a Night Midweek Special Early Check In
Lake Mary
10.0 out of 10, Exceptional, (19 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is €210
includes taxes & fees
12 Jun - 13 Jun
Charming Cottage Retreat – Just 100 a Night Midweek Special Early Check In
Exterior

Charming Historic Cottage with Cozy Porch and Garden Retreat

Charming Historic Cottage with Cozy Porch and Garden Retreat
Polk City
10.0 out of 10, Exceptional, (3 reviews)
"Clean comfort all ok"
United States
Donald P.
The price is €178
includes taxes & fees
14 Jun - 15 Jun
Charming Historic Cottage with Cozy Porch and Garden Retreat
Property grounds

Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (22 reviews)
"The setting was very nice and in a quiet area, but conveniently located to travel around Florida. Cottage was clean and very comfortable. Would definitely stay again."
United States
Brenda P.
The price is €256
includes taxes & fees
14 Jun - 15 Jun
Cozy Lake Front Cottage
House (4 Bedrooms) | Interior

Family Resort Home w Pool, BBQ & Game Room

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
Family Resort Home w Pool, BBQ & Game Room
Property grounds

Shore Steps Cottage - Walking Distance To The Town Of Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere
Windermere
The price is €333
includes taxes & fees
19 Jun - 20 Jun
Shore Steps Cottage - Walking Distance To The Town Of Windermere
Property grounds

Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"

Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Mount Dora
10.0 out of 10, Exceptional, (18 reviews)
"This was a nice charming home my weekend visit to Mount Dora - home was clean, close to downtown and host was a great communicator. "
United States
Rena C.
The price is €221
includes taxes & fees
16 Jun - 17 Jun
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Exterior

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
College Park
9.8 out of 10, Exceptional, (40 reviews)
"Our hosts were incredibly accommodating and welcoming. This was the perfect place for us to stay while in town for a wedding in Winter Park. Thank you! "
United States
Danielle S.
The price is €307
includes taxes & fees
2 Jul - 3 Jul
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Exterior

Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney

Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
Davenport
5.0 out of 10, (2 reviews)
"Needs some upgrades. The bed was a full size, very small for a couple, should really think of upgrading to a king. Pans were old and could use replacing. Bugs and ants constant. Shower was small. Very small tv. Stovetop had missing nob and was difficult to operate. Definitely needs upgrading, left a day early, didn’t feel comfortable there. "
United States
Rebecca F.
The price is €139
includes taxes & fees
12 Jun - 13 Jun
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
House (3 Bedrooms) | Interior

Davenport Basecamp! 3BR Family Home w/ Patio

Davenport Basecamp! 3BR Family Home w/ Patio
3.0 star property
Davenport
The price is €315
includes taxes & fees
24 Jun - 25 Jun
Davenport Basecamp! 3BR Family Home w/ Patio
Front of property

Mount Dora Cottages

Mount Dora Cottages
3.0 star property
Mount Dora
9.4 out of 10, Exceptional, (211 reviews)
"Perfect spot"
United States
PATRICIA
The price is €205
includes taxes & fees
23 Jun - 24 Jun
Mount Dora Cottages
Property grounds

Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
The price is €200
includes taxes & fees
18 Jun - 19 Jun
Romantic Lakefront Getaway with Balcony near Downtown Orlando
House (3 Bedrooms) | Interior

Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is €223
includes taxes & fees
14 Jun - 15 Jun
Upstay: Bright Family-friendly Retreat With Patio
Interior

Beautiful Historic Cottage, Rendezvous

Beautiful Historic Cottage, Rendezvous
Mount Dora
9.4 out of 10, Exceptional, (16 reviews)
"This property is the perfect location for walking downtown shops and dining! "
United States
Julie
Beautiful Historic Cottage, Rendezvous
Exterior

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
3.0 star property
Kissimmee
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Garden Hotel Reviews

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

8/10 Good
"Nice and affordable place but the pools do get full quickly, everything was still nice and also good security."
Lizbeth 2-night trip
Posted 1 hour ago
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
460
Accommodation
2484 Cottages
Lowest Price
€139
Highest Price
€471

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between €139 and €471 per night. These stays offer a chance to get reacquainted with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Winter Garden with Expedia?
Expedia has some great cottages in Winter Garden, so get ready for a memorable holiday on nature's doorstep. If you're sticking to a budget, select how much you'd like to spend and the preferred star rating of your property. Or, use our filters to search for cottages with free WiFi or a kitchen. We'll help you find the right fit whatever your bank balance or plans.
How can I find cheap cottages in Winter Garden?
With Expedia's convenient filter tool, scoring cheap cottages in Winter Garden has never been simpler. To discover accommodation that'll make your wallet happy, fine-tune your search results by budget, star rating and amenities.
What is there to do in Winter Garden near my cottage?
Whatever you're into, Winter Garden has plenty of things to keep you on the go. Orange County National Golf Club, Resurrection Catholic Church and West Orange Trail are on many travellers' agendas. Don't forget to explore Winter Garden Art Association, Winter Garden Heritage Museum and Oakland Nature Preserve either. With Expedia's Winter Garden hotel deals, you'll be able to see more renowned attractions like these with the cash you save.